Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C

Journal of Natural Products

Volumn 74, Issue 3, 2011, Pages 357-364

  Yamashita, Shuji ^a   Ishihara, Yuuki ^a   Morita, Hiroyuki ^a   Uchiyama, Junichi ^a   Takeuchi, Katsutoshi ^a   Inoue, Masayuki ^a,b   Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CIGUATOXIN; POLYETHER; SULFOXIDE; VINYL DERIVATIVE;

ARTICLE; CYCLIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

CIGUATERA POISONING; CIGUATOXINS; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SEAFOOD; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFOXIDES; VINYL COMPOUNDS;

CIGUATERA;

EID: 79953236568     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100729d     Document Type: Article

References (68)

1. Lewis, R. J. Toxicon 2001, 39, 97-106.
2. (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
3. (b) Scheuer, P. J. Tetrahedron 1994, 50, 3-18.
4. Yasumoto, T.; Nakajima, I.; Bagnis, R.; Adachi, R. Bull. Jpn. Soc. Sci. Fish. 1977, 43, 1015-1026.
5. (a) Murata, M.; Legrand, A.-M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929-8931.
6. (b) Murata, M.; Legrand, A.-M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386.
7. (a) Yasumoto, T.; Igarashi, T.; Legrand, A.-M.; Cruchet, P.; Chinain, M.; Fujita, T.; Naoki, H. J. Am. Chem. Soc. 2000, 122, 4988-4989.
8. (b) Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975-1978.
9. (c) Satake, M.; Fukui, M.; Legrand, A.-M.; Cruchet, P.; Yasumoto, T. Tetrahedron Lett. 1998, 39, 1197-1198.
10. Yasumoto, T.; Fukui, M.; Sasaki, K.; Sugiyama, K. J. AOAO Int. 1995, 78, 574-582.
11. For recent research on ciguatera and marine toxins, see: Special issue on "Ciguatera and Related Biotoxins". Toxicon 2010, 56, 653-847, and references therein.
12. For recent total synthesis and synthetic studies from other groups, see: (a) Isobe, M.; Hamajima, A. Nat. Prod. Rep. 2010, 27, 1204-1226.
13. (b) Hamajima, A.; Isobe, M. Angew. Chem., Int. Ed. 2009, 48, 2941-2945.
14. (c) Fuwa, H.; Fujikawa, S.; Tachibana, K.; Takakura, H.; Sasaki, M. Tetrahedron Lett. 2004, 45, 4795-4799.
15. Fujiwara, K.; Goto, A.; Sato, D.; Ohtaniuchi, Y.; Tanaka, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2004, 45, 7011-7014.
16. (e) Domon, D.; Fujiwara, K.; Ohtaniuchi, Y.; Takezawa, A.; Takeda, S.; Kawasaki, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 8279-8283.
17. (f) Domon, D.; Fujiwara, K.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 8285-8288.
18. (g) Takizawa, A.; Fujiwara, K.; Doi, E.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron 2006, 62, 7408-7435.
19. (h) Hamajima, A.; Isobe, M. Org. Lett. 2006, 8, 1205-1208.
20. (i) Nonoyama, A.; Hamajima, A.; Isobe, M. Tetrahedron 2007, 63, 5886-5894.
21. (j) Clark, J. S.; Conroy, J.; Blake, A. J. Org. Lett. 2007, 9, 2091-2094.
22. (k) Goto, A.; Fujiwara, K.; Kawai, A.; Kawai, H.; Suzuki, T. Org. Lett. 2007, 9, 5373-5376.
23. (l) Kadota, I.; Abe, T.; Uni, M.; Takamura, H.; Yamamoto, Y. Tetrahedron Lett. 2008, 49, 3643-3647.
24. (m) Kadota, I.; Abe, T.; Uni, M.; Takamura, H.; Yamamoto, Y. Tetrahedron 2009, 65, 7784-7789.
25. (a) Hirama, M.; Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904-1907.
26. (b) Inoue, M.; Uehara, H.; Maruyama, M.; Hirama Org. Lett. 2002, 4, 4551-4554.
27. (c) Inoue, M.; Miyazaki, K.; Uehara, H.; Maruyama, M.; Hirama, M. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 12013-12018.
28. (d) Inoue, M.; Hirama, M. Synlett 2004, 577-595.
29. (e) Inoue, M.; Hirama, M. Acc. Chem. Res. 2004, 37, 961-968.
30. (f) Hirama, M. Chem. Rec. 2005, 5, 240-250.
31. (g) Inoue, M.; Miyazaki, K.; Ishihara, Y.; Tatami, A.; Ohnuma, Y.; Kawada, Y.; Komano, K.; Yamashita, S.; Lee., N.; Hirama, M. J. Am. Chem. Soc. 2006, 128, 9352-9354.
32. (a) Inoue, M.; Lee, N.; Miyazaki, K.; Usuki, T.; Matsuoka, S.; Hirama, M. Angew. Chem., Int. Ed. 2008, 47, 8611-8614.
33. (b) Ishihara, Y.; Lee, N.; Oshiro, N.; Matsuoka, S.; Yamashita, S.; Inoue, M.; Hirama, M. Chem. Commun. 2010, 46, 2968-2970.
34. (a) Oguri, H.; Hirama, M.; Tsumuraya, T.; Fujii, I.; Maruyama, M.; Uehara, H.; Nagumo, Y. J. Am. Chem. Soc. 2003, 125, 7608-7612.
35. (b) Tsumuraya, T.; Fujii, I.; Inoue, M.; Tatami, A.; Miyazaki, K.; Hirama, M. Toxicon 2006, 48, 287-294.
36. (c) Tsumuraya, T.; Fujii, I.; Hirama, M. Toxicon 2010, 56, 797-803.
37. (a) Yamaoka, K.; Inoue, M.; Miyahara, H.; Miyazaki, K.; Hirama, M. Br. J. Pharmacol. 2004, 142, 879-889.
38. (b) Yamaoka, K.; Inoue, M.; Miyazaki, K.; Hirama, M.; Kondo, C.; Kinoshita, E.; Miyoshi, H.; Seyama, I. J. Biol. Chem. 2009, 284, 7597-7605.
39. (a) Inoue, M.; Ishihara, Y.; Yamashita, S.; Hirama, M. Org. Lett. 2006, 8, 5801-5804.
40. (b) Inoue, M.; Yamashita, S.; Ishihara, Y.; Hirama, M. Org. Lett. 2006, 8, 5805-5808.
41. (a) Inoue, M.; Wang, G. X.; Wang, J.; Hirama, M. Org. Lett. 2002, 4, 3439-3442.
42. (b) Inoue, M.; Wang, J.; Wang, G. X.; Ogasawara, Y.; Hirama, M. Tetrahedron 2003, 59, 5645-5659.
43. Compounds 13a-d were synthesized from 2-deoxy-D-ribose according to the known procedures: See Supporting Information.
44. The Sasaki and Tachibana group reported that 6-exo radical cyclization of i afforded the undesired cis-substituted pyran ring iii via intermediate ii: Sasaki, M.; Inoue, M.; Noguchi, T.; Takeichi, A.; Tachibana, K. Tetrahedron Lett. 1998, 39, 2783-2786. (Chemical Equation Presented)
45. Although we attempted 6-exo radical cyclizations using O,S-acetal instead of O,Se-acetal, these afforded only little product, if any desired pyran ring. For recent examples of radical reaction using cis-vinyl sulfoxides, see: (a) Zahouly, M.; Journet, M.; Malacria, M. Synlett 1994, 388-368.
46. (b) Keum, G.; Kang, S. B.; Kim, Y.; Lee, E. Org. Lett. 2004, 6, 1895-1897.
47. (c) Jung, J. H.; Kim, Y. W.; Kim, M. A.; Choi, S. Y.; Chung, Y. K.; Kim, T.-R.; Shin, S.; Lee, E. Org. Lett. 2007, 9, 3225-3228.
48. (d) Kimura, T.; Hagiwara, M.; Nakata, T. Tetrahedron Lett. 2007, 48, 9171-9175.
49. (e) Jung, J. H.; Lee, E. Angew. Chem., Int. Ed. 2009, 48, 5698-5700.
50. (f) Kimura, T.; Hagiwara, M.; Nakata, T. Tetrahedron 2009, 65, 10893-10900.
51. See Supporting Information.
52. (a) Maruyama, M.; Inoue, M.; Oishi, T.; Oguri, H.; Ogasawara, Y.; Shindo, Y.; Hirama, M. Tetrahedron 2002, 58, 1835-1851.
53. (b) Kobayashi, S.; Takahashi, Y.; Komano, K.; Alizadeh, B. H.; Kawada, Y.; Oishi, T.; Tanaka, S.; Ogasawara, Y.; Sasaki, S.; Hirama, M. Tetrahedron 2004, 60, 8375-8396.
54. Manuel, P.; Pilar, C.; Generosa, G.; Carmen, T.; Yagamare, F. Tetrahedron Lett. 2004, 45, 5207-5209.
55. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
56. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
57. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
58. (a) Dahamukar, V. H.; Rychnovsky, S. D. J. Org. Chem. 1996, 61, 8317-8320.
59. (b) Kadota, I.; Ohno, A.; Matsuda, K.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 6702-6703.
60. Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
61. (a) Kosugi, H.; Kitaoka, M.; Tagami, K.; Takahashi, A.; Uda, H. J. Org. Chem. 1987, 52, 1078-1082.
62. (b) Solladie, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173.
63. For a recent review on Pummerer rearrangement, see: Bur, S. K.; Padwa, A. Chem. Rev. 2004, 104, 2401-2432.
64. (a) Mukaiyama, T.; Sugaya, T.; Marui, S.; Nakatsuka, T. Chem. Lett. 1982, 11, 1555-1558.
65. (b) McAuliffe, J. C.; Hindsgaul, O. Synlett 1998, 307-309.
66. (a) Gaunt, M. J.; Yu, J.; Spencer, J. B. J. Org. Chem. 1998, 63, 4172-4173.
67. (b) Xia, J.; Abbas, S. A.; Locke, R. D.; Piskorz, C. F.; Alderfer, J. L.; Matta, K. L. Tetrahedron Lett. 2000, 41, 169-173.
68. (c) Wright, J. A.; Yu, J.; Spencer, J. B. Tetrahedron Lett. 2001, 42, 4033-4036.